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Featured Vacation Homes in Chesterfield

Beautiful Historic Home Near Downtown With Off-street Parking
Beautiful Historic Home Near Downtown With Off-street Parking
St. Louis, MO
At this vacation home, guests have access to a garden.
Vintage French Beauty - Newly Renovated & Spacious
Vintage French Beauty - Newly Renovated & Spacious
St. Charles, MO
This vacation home is a smoke-free vacation home.
Southwest-charming South City Home-close to all in Stl!
Southwest-charming South City Home-close to all in Stl!
St. Louis, MO
At this vacation home, guests have access to a garden.
Soulard La Maison Renovated Jacuzzi Tub Fireplace
Soulard La Maison Renovated Jacuzzi Tub Fireplace
St. Louis, MO
$99
At this vacation home, guests have access to a spa tub.
Delmar 1st Floor · Luxury Unit 1st Floor: Walk to Downtown Clayton
Delmar 1st Floor · Luxury Unit 1st Floor: Walk to Downtown Clayton
St. Louis, MO
This vacation home is a smoke-free vacation home.
Historic/renovated Smart Home Fireplace Yard
Historic/renovated Smart Home Fireplace Yard
St. Louis, MO
$99
At this vacation home, guests have access to barbecue grills.
Lake Haven--updated Mid Century Cabin Only 35 Mins From St Louis
Lake Haven--updated Mid Century Cabin Only 35 Mins From St Louis
Pacific, MO
Guests staying at this vacation home have access to a garden and barbecue grills.
Airbnb, Micro Weddings, Receptions, Special Honeymoon/bridal Suite
Airbnb, Micro Weddings, Receptions, Special Honeymoon/bridal Suite
Pacific, MO
$175
This vacation home features a water park and a garden.
Bird Haus - on Main Street, Katy Trail, Near Lindenwood
Bird Haus - on Main Street, Katy Trail, Near Lindenwood
St. Charles, MO
$110
At this vacation home, guests have access to a garden.
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Chesterfield Vacation Homes

Book vacation homes in Chesterfield
Next time you take a group getaway top Chesterfield, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Chesterfield vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Chesterfield vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Chesterfield; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Chesterfield rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Chesterfield is sure to be a winner.

Hotel Options in Chesterfield

See all 1,079 Properties in Chesterfield
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.